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A 1999 Cannondale Silk Road Saeco bike.

The story goes that one day Joe Montgomery was watching a long-haired fellow pedaling his bike up a hill while lugging a heavy backpack. “He said, ‘God, that’s a crazy way to get around,’ ” Montgomery’s son, Scott, recalls. That moment inspired the creation of Cannondale, a brand that’s still renowned throughout the worldwide bicycling community 50 years later.

The year was 1971, and in rented loft space above a pickle factory near the Cannondale railroad station in Wilton, Joe Montgomery and his small research and development team conceived the idea for a bicycle-towed trailer that became known as “the Bugger.” The tiny company that initially focused on making bicycling accessories and clothing would challenge the industry orthodoxy in the 1980s by rolling out some of the first mass-produced bicycle frames made from aluminum instead of steel.

Cannondale went on to burnish its reputation for innovation through sponsorship of championship racing teams and continues to hold a place among avid cyclists as a premium brand.

A hometown brand

Decades after Cannondale went international — and following an ill-fated side trip into motorcycles that bankrupted the company and ended the Montgomery family’s ownership — the brand’s local presence continues in the town where it all started.

Cannondale quickly outgrew its original Wilton offices, moving to Georgetown and later Bethel. In 2013, it moved back to Wilton, opening its 51,000-square-foot global headquarters at 1 Cannondale Way. “At one time Cannondale was making all of L.L. Bean’s dog beds,” Montgomery says, recalling the evolution of the brand. He did assembly work as a 10-year-old and stuck around to launch the company’s European operation in 1988.

The first Cannondale bike was the ST-500, an aluminum touring model, “and that was mainly done because Cannondale had made all those bike bags, so it was known as a brand that was ideal for touring; you could ride it all the way across the country,” Montgomery says.

The concept of using lighter, stiffer aluminum was the brainchild of an engineer from one of the nearby submarine builders. “At first, nobody wanted them, or very few, because it was considered odd-looking. At the time, all the European steel frames for brands like Bianchi and Peugeot — those were all the ones that everybody wanted,” Montgomery says.

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A Cannondale advertisement from 1990.

The company soon jumped into the burgeoning mountain biking field, designing off-road models for racers and enthusiasts. “When people tried it, it was, ‘Wow, this is different, this is better,’ ” says Murray Washburn, Cannondale’s director of product marketing. “If you rode a steel bike and you rode a Cannondale, it was a completely different feel that even somebody who’s not a super-experienced cyclist could feel immediately.”

Cannondale’s sponsorship of the Italian Saeco racing team and its legendary sprinter Mario Cipollini helped legitimize the company’s 10-speed road bikes among serious road cyclists — the same way forming the Volvo-Cannondale mountain bike team drove the popularity of its off-road bikes.

‘Restless, maverick spirit’

Joe Montgomery instilled a “restless, maverick spirit” that fueled an appetite for risk, culminating in revolutionary designs and manufacturing operations, Washburn says. “Everything is possible, take risks, push things,” was Joe Montgomery’s philosophy, recalls Washburn, who has worked at Cannondale since the late 1990s. Even the failed venture into motorcycles that drove Cannondale into bankruptcy in 2003 was very much in character. “We had grown so much that we needed to look elsewhere to continue to grow the company, and that continual hunger of ‘Is there a better way?’ led into the motorsports thing,” Washburn says.

The cash crunch sent Cannondale into the hands of its largest creditor, Pegasus, but the brand’s popularity among bicyclists was going strong, with the emergence of carbon-fiber frames and other advances gaining momentum. “We actually came out of bankruptcy with more bike dealers than when we went into bankruptcy,” Washburn says.

Pegasus sold Cannondale to the Canadian company Dorel Industries in 2008. Another ownership came just this past October, as Dorel sold Cannondale to Pon Holdings, a Dutch company with an existing lineup of performance bikes, including Cervelo, Focus and Santa Cruz, in a deal worth $810 million.

The legend lives on

The brand’s early models retain their legendary status among scores of hardcore passionistas on social media pages and websites like VintageCannondale, where riders swap stories and photos.

Joe Montgomery, now 81, lives in Florida where he runs a software company, his son says. Cannondale’s founder “keeps an eye on the company the same way a retired baseball coach might follow an old protégé through the leagues,” according to an archival history published by Cannondale.

Years after his family’s ties to the company ended, Scott Montgomery runs a marketing company geared toward outdoor brands and maintains his passion for cycling. “I still love it as an industry and I’m happy to see the company make that milestone,” says Scott, now 60. “It’s a household name within the category of performance bicycles worldwide, so it’s a proud moment.”

The future of biking

While some enthusiasts feel its corporate parentage has put the brakes on Cannondale’s pioneering spirit, Washburn does not believe that’s the case. “The push to be different and disruptive is less, but the appetite for out-of-the-box thinking is still there,” he says.

Cannondale’s sales are almost evenly split between road and mountain models, Washburn says. And the company has jumped into the cycling boom that accelerated during the pandemic, including electric models under the nameplate Neo, like the Adventure Neo. “The effect on the market of e-bikes cannot be overstated,” Washburn says. “It’s bringing new people who wouldn’t ordinarily be thinking about riding a bike into cycling, whether it’s for transportation or recreation. It’s making the riding experience and the possibility of not using a car so much easier, making mountain and road biking more accessible to people.

“The industry has grown up and so has Cannondale,” Washburn adds. “We’re not focusing on the wild and attention-getting things of the past. We’re focusing on things that will make a real difference in people’s rides, making it easier to use the bikes and service them.”

This article appears in the December 2021 issue of Connecticut MagazineYou can subscribe to Connecticut Magazine here, or find the current issue on sale hereSign up for our newsletter to get our latest and greatest content delivered right to your inbox. Have a question or comment? Email editor@connecticutmag.com. And follow us on Facebook and Instagram @connecticutmagazine and Twitter @connecticutmag.